Methyl 4-(4-oxo-chroman-3-ylidenemethyl)-benzoate → Methyl 4-chroman-3-ylmethyl-benzoate

HRID 252763

Reaktionsgleichung

Reaktionsgleichung von HRID 252763
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][C:3]1=[CH:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1>CO.CC(N(C)C)=O.[Pd]>[O:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2][CH:3]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=2)[CH2:4]1

Komponenten

5

Edukt 1

HCID 4240115Methyl 4-(4-oxo-chroman-3-ylidenemethyl)-benzoate

Produkt 1

HCID 22478793Methyl 4-chroman-3-ylmethyl-benzoateAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

Pd/C 10% was added to a suspension of 260 (200 mg, 0.68 mmol) in MeOH (40 ml) and DMA (10 ml) which was previously purged under vacuum. The reaction mixture was stirred during 4 h at room temperature. After evaporation of the MeOH, water was added to the oily residue and the precipitate obtained was filtered. The crude residue was then purified by flash chromatography on silica gel (5-8% AcOEt/Hex) to afford the title compound 263 (114 mg, 59%) as a white solid. LRMS: 282.1 (Calc.); 283.0 (found).

Aufarbeitung

  1. customwas previously purged under vacuum
  2. customAfter evaporation of the MeOH, water
  3. additionwas added to the oily residue
  4. customthe precipitate obtained
  5. filtrationwas filtered
  6. customThe crude residue was then purified by flash chromatography on silica gel (5-8% AcOEt/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-45ed9d5bd5034c37a26588f60357fb8a
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868204B2

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